Homes for Sale near Middletown High School

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  /38

  $469,900

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft

  95 Training Hill Rd, Middletown, CT 06457

  Welcome to 95 Training Hill Road - Where Comfort Meets Convenience in Middletown! Discover this beautifully updated ranch-style gem in one of Middletown's most desirable areas. Featuring 4 spacious bedrooms and 2 full bathrooms, this home is perfect for anyone seeking style, space, and functionality. Step inside to an inviting open floor plan that flows effortlessly from room to room - ideal

  

  Guillermo Araujo

  Five Stars Realty

  (860) 891-2298

  95 Training Hill Rd, Middletown, CT 06457
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• 

  

  

  /32

  $459,900 Open Mon 10:30AM - 12:30PM

  • 4 Beds
  • 3 Baths
  • 1,923 Sq Ft

  112 Rolling Green, Middletown, CT 06457

  Welcome to this spacious 4-bedroom, 3-full-bath Cape nestled in a thoughtfully planned neighborhood perfect for evening strolls and dog walking. Set on a generously sized lot offering both privacy and tranquility, this home blends peaceful living with unmatched convenience. Enjoy the ease of access to major highways while still savoring the comfort of a secluded setting. With flexible living

  Tanya Bottaro Real Broker CT, LLC

  112 Rolling Green, Middletown, CT 06457
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  /37

  $529,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,198 Sq Ft

  1037 Bartholomew Rd, Middletown, CT 06457

  Welcome to 1037 Bartholomew Rd in Middletown, CT - a single-level ranch that keeps things simple, practical, and just a little bit charming (without trying too hard). With 4 bedrooms, 2.5 baths, and 1,758 square feet of living space, this 1969-built home has seen some updates that matter: a refreshed kitchen and bathrooms, and new flooring in the rooms you actually use the most. The main level

  Devon Taylor Assael Dave Jones Realty, LLC

  1037 Bartholomew Rd, Middletown, CT 06457
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  /39

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  152 Brainard Hill Rd, Higganum, CT 06441

  Set back from the road, this home offers the perfect blend of modern design and natural surroundings. As you arrive via the bridge crossing over a roaring brook, you'll immediately appreciate the thoughtfully landscaped grounds with mature trees and colorful perennials. Inside, the home impresses with high ceilings throughout the foyer and living areas that fill the space with natural light. The

  Lisa Romano William Pitt Sotheby's Int'l

  152 Brainard Hill Rd, Higganum, CT 06441
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  /35

  $399,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  158 Higby Rd, Middletown, CT 06457

  Welcome to this charming Ranch with 3 Bedrooms, 2 Full Baths, Finished Basement, Attached Garage and Private Backyard Retreat. It is conveniently located in the northern end of Middletown off of East St and near the picturesque Wadsworth Falls State Park. This home offers serene living with a deck off the kitchen, 3 season sunroom, and walkout basement. The main level features hardwood floors

  Elizabeth Harrison Hagel & Assoc. Real Estate

  158 Higby Rd, Middletown, CT 06457
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  /38

  $429,999

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  106 Lorraine Terrace, Middletown, CT 06457

  COMPLETELY RENOVATED WOODLAND OASIS IN SOUGHT-AFTER WESTFIELD! This stunning split-level home sits on a private 0.47-acre lot blending modern luxury with natural charm. Freshly painted inside and out with new architectural roof and high-efficiency central AC. The showstopping kitchen features white-shaker cabinetry, granite countertops, stainless appliances, and herringbone blue tile backsplash.

  Romanee Ives Cornerstone Homes Plus, Inc.

  106 Lorraine Terrace, Middletown, CT 06457
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  /40

  $580,000

  • 4 Beds
  • 3.5 Baths
  • 3,756 Sq Ft

  36 Mcgrath Dr, Middletown, CT 06457

  Welcome to your dream home! This spacious Colonial offers the perfect blend of comfort, style, and convenience. Inside, you'll find a thoughtfully designed layout ideal for both entertaining and everyday living. The main floor features a bright, eat-in kitchen, a formal dining room for special occasions, a cozy living room, a welcoming family room, and a private office - all complemented by a

  Tom Derick Executive Real Estate Inc.

  36 Mcgrath Dr, Middletown, CT 06457
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  /29

  $397,000

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  20 Mulberry Ln, Middletown, CT 06457

  Charming Colonial in a Desirable Neighborhood Don't miss this amazing opportunity to own a charming colonial in a highly sought-after neighborhood! Nestled in a peaceful cul-de-sac, this cozy, well-maintained home offers a space efficient floor plan and is part of a planned unit development (PUD). This home also includes a weather protected entrance on an inviting front porch. The first floor

  Noreen Sinclair Berkshire Hathaway NE Prop.

  20 Mulberry Ln, Middletown, CT 06457
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  /38

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  613 Ridgewood Rd, Middletown, CT 06457

  Exceptionally maintained 4 bedroom, 2.5 bath Colonial home built in 1996 is located on a secluded 1.5 acre lot, nestled away in the Westfield neighborhood of Middletown. This property offers maximum privacy, surrounded by beautiful trees and hardly visible from the road. Upon entering the home, you immediately appreciate the open concept, hardwood flooring, wainscoting and abundance of natural

  Gregory Clancy eXp Realty

  613 Ridgewood Rd, Middletown, CT 06457
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  /40

  $589,999

  • 4 Beds
  • 2.5 Baths
  • 2,813 Sq Ft

  16 Snow Ridge S, Middletown, CT 06457

  Nestled near the top of highly desirable Westfield Hills on a private cul-de-sac, this bright, oversized Colonial offers space, comfort, and charm. With 4 bedrooms-including a spacious master suite with a walk-in closet, large office, and private bath with jacuzzi tub and shower-this home is built for relaxed living. A second full bath completes the upper level. Downstairs, the open layout is

  Bruce Bayles William Raveis Real Estate

  16 Snow Ridge S, Middletown, CT 06457
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  /20

  $475,000

  • 4 Beds
  • 1 Bath
  • 1,075 Sq Ft

  35 Boston Rd, Middletown, CT 06457

  Welcome to 35 Boston Ave, Middletown, a classic 4-bedroom Cape Cod-style home with great potential! This home offers a functional layout with two bedrooms on the first floor and two additional bedrooms upstairs, making it ideal for a variety of living arrangements. Featuring hardwood floors throughout, an eat-in kitchen, and a full unfinished basement, this home is ready for your personal touch.

  Michael Calabro Coldwell Banker Calabro

  35 Boston Rd, Middletown, CT 06457
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  /3

  $449,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  00 Villa St, Middletown, CT 06457

  DON"T SETTLE on Your Home: Take this opportunity to get the House of your Dreams... This lot has a picturesque view with over 100 feet of secluded River views (No Flood Ins. Needed) on a cul-de-sac with 120 ft. of road frontage. This lot already has an ideal home option with 3bd, 2 bath, open concept custom Kitchen (quartz countertops, Island, Tile floor), Dining room with sliders to deck area,

  Lisa Sherman My Realtor, LLC

  00 Villa St, Middletown, CT 06457
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  /11

  $399,900

  • 6 Beds
  • 2 Baths
  • 2,579 Sq Ft

  116 Front St, Middletown, CT 06457

  Welcome to this beautifully maintained & spacious side-by-side two-family home - Each unit offers generous living space, including 3 bedrooms, a walk-up attic and full basement. Enjoy hardwood floors, high ceilings, and charming original details throughout. The property features a large backyard, 2-car garage & ample off-street parking. Conveniently located near shopping, public transportation,

  Michelle Mazzotta eXp Realty

  116 Front St, Middletown, CT 06457
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  /34

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft

  234 S Main St Unit 303, Middletown, CT 06457

  Let me know your thoughts! Welcome to 234 S Main St, Unit 303-a charming 2-bedroom, 2-bath condo in a beautifully maintained building that's proudly listed on the National Register of Historic Places. With exposed brick, massive timber beams, and unique plank ceilings, this 120-year-old treasure blends timeless character with modern comfort. Inside, you'll find 1,147 sq ft of easy, one-level

  Devon Taylor Assael Dave Jones Realty, LLC

  234 S Main St Unit 303, Middletown, CT 06457
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  /16

  $169,900

  • 1 Bed
  • 1.5 Baths
  • 738 Sq Ft

  111 Dekoven Dr Unit 508, Middletown, CT 06457

  TURN KEY UNIT AT RIVER'S EDGE WITH WATER VIEWS- THIS MOVE IN READY CONDO FEATURES A FULLY APPL KIT WITH LAMINATE FLS- LIVING RM-DINING AREA WITH SLIDERS LEADING TO A BALCONY OVERLOOKING THE CT RIVER- LARGE BDRM WITH A FULL BATH & WALK IN CLOSET- 1.5 TOTAL BATHS- COMMON FEE INCLS HEAT, HW, AC, WATER & SEWER, POOL, GYM, COMMUNITY RM & A STORAGE AREA FOR PERSONAL BELONGINGS- NO PETS-

  Michael Vitale Vitale Realty

  111 Dekoven Dr Unit 508, Middletown, CT 06457
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  /36

  $269,900

  • 2 Beds
  • 1.5 Baths
  • 1,306 Sq Ft

  2 Butternut Knolls Unit 2, Middletown, CT 06457

  Rarely available Townhouse style condo in Butternut Knoll with fantastic location near Wesleyan and vibrant Downtown! This bright and sunny unit features nicely sized bedrooms with high ceilings and double closets, skylight, private patio, central heat and air plus garage parking. The main floor includes a roomy living area with bay window and breakfast bar. The kitchen includes a dining area

  Pauline Webb William Raveis Real Estate

  2 Butternut Knolls Unit 2, Middletown, CT 06457
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  /31

  $289,900 Open Sun 11:30AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,601 Sq Ft

  65 Stevens Ln, Middletown, CT 06457

  Run do not walk to see this amazing story book home. Extremely versatile offering 2 bedrooms on the first floor with a full bath and 2 bedrooms upstairs with additional full bath. This picturesque Cape sits a beautiful level landscaped lot offering magnificent center patio with pergola draped with mature grape vines. Perfect for all your outdoor entertaining and Barbecue's. The interior of this

  Mark Toledo Berkshire Hathaway NE Prop.

  65 Stevens Ln, Middletown, CT 06457
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  /35

  $315,000

  • 3 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  22 In Town Terrace Unit 22, Middletown, CT 06457

  Welcome to The Pines at Indian Woods, unit 22-a beautifully appointed, contemporary 3 bedroom, 2.5 bathroom residence nestled in the vibrant heart of Middletown, CT. This meticulously maintained home spans approximately 1388 square feet and effortlessly blends modern elegance with everyday comfort. As you step inside, you'll be greeted by a bright, airy interior with plenty of natural light. The

  Agota Perry-Hill William Raveis Real Estate

  22 In Town Terrace Unit 22, Middletown, CT 06457
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  /21

  $379,000

  • 6 Beds
  • 3 Baths
  • 2,480 Sq Ft

  35 Clinton Ave, Middletown, CT 06457

  **OPPORTUNITY**Sidewalk lined neighborhood with this well cared for 3 family home resting at the end of the street! Fully fenced, large, covered patio in the backyard, plenty of paved off street parking, detached 3 car garage & more! Lower level is unfinished, great for storage & laundry! All units feature 2 bedrooms, 1 full bath, kitchen & living room! 1st floor with a covered porch & 2nd floor

  Eugene Kirouac Premier Re Group LLC

  35 Clinton Ave, Middletown, CT 06457
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  /12

  $127,500

  • 1 Bed
  • 1 Bath
  • 579 Sq Ft

  117 Burgundy Hill Ln Unit 117, Middletown, CT 06457

  Want to be the first to live in this total rebuilt condominium?? This building at Peppermill Village was where there was a fire in February of 2024 that destroyed many units. Insurance and Association rebuilt building and now ready for occupancy. Unit offers 1 bedroom that is carpeted, has laminate in Livingroom and kitchen, New everything. Owner putting stainless steel appliances in the next

  Kerry Hart William Raveis Real Estate

  117 Burgundy Hill Ln Unit 117, Middletown, CT 06457
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  /12

  $449,900 Open Sun 2PM - 4PM

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft

  23 Silver St, Middletown, CT 06457

  Take advantage of this chance to own a versatile multi-unit property that combines space, flexibility, and strong investment potential. Whether you're planning to live in one unit and rent out the other or fully lease the entire property, this is an excellent opportunity to build long-term equity. Each unit features generous living areas and spacious bedrooms-perfect for attracting reliable

  Yvonne Bailey I'Lann Realty, LLC

  23 Silver St, Middletown, CT 06457
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  /33

  $220,000

  • 4 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  192 Rising Trail Dr, Middletown, CT 06457

  There's space for all in this well-cared for three-level 4 bedroom townhouse with under-unit garage! The living room with dining area has a slider that opens to the deck overlooking the peaceful lawn and wooded area. The kitchen with a sunny bay window offers plenty of cabinetry. The second level features convenient upper-level laundry, and two bedrooms including the primary suite with walk-in

  Siobhan McLaughlin William Raveis Real Estate

  192 Rising Trail Dr, Middletown, CT 06457
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  /36

  $350,000

  • 4 Beds
  • 1.5 Baths
  • 2,042 Sq Ft

  191 Long Hill Rd, Middletown, CT 06457

  Step into timeless charm with this delightful 4-bedroom home, one and a half baths, and 2,042 square feet of living space. Set on a level 0.46-acre lot surrounded by beautiful countryside, this circa-1860 gem is full of character and ready for your personal touch. Enjoy peaceful views and outdoor strolls with a lovely walking path just across the street. The location is convenient to all your

  Carol Farmer William Raveis Real Estate

  191 Long Hill Rd, Middletown, CT 06457
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  /34

  $350,000

  • 5 Beds
  • 2 Baths
  • 2,275 Sq Ft

  8 Batt St, Middletown, CT 06457

  Discover 8 Batt St, Middletown, CT-a stunning 5-bed, 2-bath ranch blending single-level ease with modern updates. Nestled in a quiet, family-friendly area, this move-in-ready home offers comfort and style. Step into a bright foyer leading to a spacious living room with hardwood floors and large windows. The updated kitchen boasts stainless steel appliances, quartz counters, a breakfast nook, and

  Luke Florian SSG Real Estate LLC

  8 Batt St, Middletown, CT 06457
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  /14

  $374,900

  • 7 Beds
  • 4 Baths
  • 2,236 Sq Ft

  68 High St, Middletown, CT 06457

  Two family home rented until March 2026! Immediate investment opportunity! Large 2-unit home located within a few minutes of Wesleyan University and downtown Middletown! Tenants pay for their own heat and hot water too! Well maintained home that you'll be proud to add to your investment portfolio!

  Dawn Satagaj William Raveis Real Estate

  68 High St, Middletown, CT 06457
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  /13

  $399,900

  • 11 Beds
  • 4 Baths
  • 5,039 Sq Ft

  84 High St, Middletown, CT 06457

  Captivating original woodwork throughout this home! Dining room with built-ins, great wood floors and room after room! There are 10 bedrooms in unit #1! Currently used as a rental property, this home could continue as a solid investment, but, would make a spectacular home for someone looking to bring this beauty back to glory! This location is ideal for anyone! Walk to downtown Middletown and

  Dawn Satagaj William Raveis Real Estate

  84 High St, Middletown, CT 06457
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  /37

  $362,500

  • 4 Beds
  • 2 Baths
  • 1,290 Sq Ft

  570 Atkins St, Middletown, CT 06457

  Must see updated ranch located in desirable Westfield section of Middletown. The town lists house as having 3 bedrooms but has a possible 4th bedroom/office in the finished walkout basement along with a spacious family room with view and access to patio and your private back yard. The kitchen opens to living room creating a very functional great room. Laundry is located on the main floor. The

  Francine McKiernan Clermont Real Estate

  570 Atkins St, Middletown, CT 06457
• 

  

  /18

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,001 Sq Ft

  35 Thayer Rd, Higganum, CT 06441

  Discover the potential of this classic 3-bedroom, 1-bath ranch nestled in the heart of Higganum. Built in 1948, this home offers just over 1,000 square feet of living space and is brimming with opportunity for the right buyer to make it shine once again. Set on a level lot, the property features vinyl siding and a detached 1-car garage for added convenience. Step inside to find hardwood floors

  Jolanta Rojek eXp Realty

  35 Thayer Rd, Higganum, CT 06441
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  /28

  $249,900 Open Sun 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  120 Saybrook Rd, Middletown, CT 06457

  Welcome to 120 Saybrook Road in Middletown-a delightful 2-bedroom, 1-bath home offering 1,008 square feet of comfortable living space. Perfectly situated for easy access to shopping, dining, major highways, and more, this home is ideal for anyone seeking a blend of charm and convenience. Step inside to find a warm, inviting layout with plenty of natural light and cozy living areas. The kitchen

  Sean Doran William Raveis Real Estate

  120 Saybrook Rd, Middletown, CT 06457
• 

  

  /17

  $125,000

  • 1 Bed
  • 1 Bath
  • 729 Sq Ft

  264 Burgundy Hill Ln, Middletown, CT 06457

  Welcome to your own peaceful retreat-where comfort meets convenience! 1-bedroomw- loft, ranch-style condo, ideally situated in the desirable Westfield Fire District. Step into a spacious open-concept living and dining area, where sliding doors lead to your private deck-perfect for morning coffee or unwinding after a long day. Whether you're looking for a low-maintenance owner-occupied home or a

  Amy Rio Executive Real Estate Inc.

  264 Burgundy Hill Ln, Middletown, CT 06457
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  /9

  $255,000

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  15 Wall St, Middletown, CT 06457

  Step into this generously sized Colonial, offering four spacious bedrooms and a flexible floor plan. The inviting living room flows seamlessly into a formal dining room-perfect for entertaining. Enjoy cooking in the large eat-in kitchen, complete with sliders that lead out to a private deck, ideal for outdoor dining and relaxation. Upstairs, you'll find four well-proportioned bedrooms, providing

  Lisa Sader-Goede Aspen Realty Group

  15 Wall St, Middletown, CT 06457
• 

  

  /13

  $360,000

  • 6 Beds
  • 3 Baths
  • 2,622 Sq Ft

  23 Portland St, Middletown, CT 06457

  This is a fantastic, possible owner-occupied investment opportunity! This spacious 3 family house with back yard is available now, in heart of downtown Middletown. The 2nd and 3rd floors are already rented, providing immediate income. The 2nd-floor kitchen has been recently renovated with updated counters and cabinets. Each unit has separate electrical panels, boilers, and water heaters, all of

  Sacha Armstrong William Pitt Sotheby's Int'l

  23 Portland St, Middletown, CT 06457
• 

  

  /20

  $299,999

  • 4 Beds
  • 1.5 Baths
  • 1,415 Sq Ft

  10 Silver St, Middletown, CT 06457

  Welcome to 10 Silver Street in Middletown! This charming colonial featuring a newer roof, brand new gas boiler, newer windows, wood floors, has been freshly painted and is move-in ready. The main floor boasts an oversized kitchen, a bright living room, a half bath, and a versatile flex space that can be used as an office, additional bedroom, or family room. Upstairs, you'll find three generously

  Sacha Armstrong William Pitt Sotheby's Int'l

  10 Silver St, Middletown, CT 06457
• 

  

  /23

  $194,900

  • 2 Beds
  • 1 Bath
  • 791 Sq Ft

  21 Portland St, Middletown, CT 06457

  Packed with character and smart updates, this charming 2-bedroom, 1-bath Colonial offers a fantastic opportunity for first-time buyers, investors, or anyone seeking a manageable and affordable home in a central location. Built in 1900 and offering 871 square feet of well-used space, this home proves that good things really do come in small packages. Inside, you'll find a comfortable and

  Amy Rio Executive Real Estate Inc.

  21 Portland St, Middletown, CT 06457
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  /38

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,214 Sq Ft

  156 S Main St, Middletown, CT 06457

  Pull into the long private driveway-room for 6-8 cars-and you'll feel the instant charm of this beautifully renovated brick two-family. The inviting front porches and classic brick facade are paired with new vinyl siding and dual-pane windows, blending timeless curb appeal with smart energy efficiency. Behind the home, a flat level lot offers a peaceful green space and a two-car garage just

  Alan Stewart Jr. ASJ Realty Partners

  156 S Main St, Middletown, CT 06457
• 

  

  /15

  $299,900

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft

  80 Prospect St, Middletown, CT 06457

  Discover a fantastic opportunity at 80 Prospect Street! This beautifully remodeled 2-family home in the heart of Middletown boasts newer mechanicals and brand-new appliances in both units, perfect for comfortable living or rental income. The 3-car garage is great for storage or the car enthusiast, and yet the home still has ample off-street parking. The second floor unit has a partially finished

  Paul Magliochetti Coldwell Banker Realty

  80 Prospect St, Middletown, CT 06457
• 

  

  /39

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  5 Westmont Dr, Middletown, CT 06457

  Conveniently located close to Wesleyan University and just minutes from downtown Middletown, this beautifully updated home offers a perfect blend of comfort and potential. The main level features a spacious primary bedroom with a full bath, providing ease and accessibility. Upstairs, you'll find two additional bedrooms with gleaming hardwood floors. The eat-in kitchen has new SS appliances,

  Natuzza Dimasi William Raveis Real Estate

  5 Westmont Dr, Middletown, CT 06457
• 

  

  /7

  $230,000

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  52 Rising Trail Dr, Middletown, CT 06457

  Spacious townhouse in the charming and cozy Beacon Hills condo community. Conveniently located minutes from major highways, public transportation, shopping centers, restaurants, medical facilities, downtown Middletown, and the Wesleyan University campus. The property offered "As Is". Subject to short sale approval. Short Sale Rider & As Is Riders must be included with the Purchase Offer.

  Thomas Galvin Precision Realty LLC

  52 Rising Trail Dr, Middletown, CT 06457
• 

  

  /24

  $299,000 Open Sun 2PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  71 E Main St, Middletown, CT 06457

  This four unit brick building sits on a corner lot within very close proximity to downtown Middletown. A vacant commercial space on the ground level provides a potential owner operator with tremendous opportunity. Three residential units fill the upper two floors including a one bedroom, two bedroom, and three bedroom apartment. The commercial space was once operated as a bar/restaurant and

  Connor Wenchell VC Property Group, LLC

  71 E Main St, Middletown, CT 06457
• 

  

  /18

  $210,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  3 Linden St, Middletown, CT 06457

  A single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

  Thomas Mele Dorrance Realty

  3 Linden St, Middletown, CT 06457

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